Heirloom Tomatoes
A Montana Travelogue
Tuesday, May 5 - Day 4
Whitefish Lodge
Facilitation days are strange.
You wake up knowing you are about to spend eight straight hours paying attention at a level that feels almost athletic. By the end of the day, your nervous system has essentially completed CrossFit for empathy.
And because this was a retreat with leaders responsible for holding culture inside genuinely turbulent times, the emotional stakes felt high from the beginning.
I should probably be careful here.
Not because anything dramatic or scandalous happened. No one flipped tables or resigned face-first into a quinoa salad. But because confidentiality matters, and the specifics are less important than the human dynamics underneath them.
What I can say is this:
There comes a moment in certain rooms when people decide whether they are actually going to tell the truth.
Not performative honesty or therapeutic jargon disguised as courage. The scarier thing.
Thoughtful honesty with actual stakes attached.
The strange thing was that here we were in one of the most beautiful places in the country, surrounded by mountains and lake water and pine trees, and we spent the day inside a conference room with no windows.
Not rustic lodge energy either.
No soaring beams or stone fireplaces. No cinematic Montana majesty.
Just fluorescent lighting, brown-beige carpeting, slightly uncomfortable banquet chairs, folding tables arranged in practical configurations, and the unmistakable atmosphere of “regional insurance training seminar.”
Even the snacks somehow felt beige.
Which may have made the emotions stand out more sharply.
There is something disorienting about discussing vulnerability beneath fluorescent lighting. Human beings are simply not designed to reveal their deepest organizational frustrations while seated in stackable conference chairs holding slightly stale granola bars.
And yet somewhere around late morning, the room changed.
Not dramatically at first.
A few longer pauses.
People looking down before speaking.
Someone folding and unfolding the edge of a nametag while another person stared at their coffee cup a little too long.
You could feel people deciding whether or not they were actually going to say the thing.
What complicated matters was that the leader of the group genuinely wanted honesty. She had worked hard to create conditions where people could speak openly. She invited direct feedback, which sounds wonderful until the direct feedback actually arrives.
Then suddenly everyone discovers they were hoping for slightly gentler honesty.
As the conversation deepened, people began offering thoughtful but difficult reflections about leadership, communication, organizational culture, and exhaustion. Nothing cruel. Nothing theatrical. But real enough that the air in the room began to tighten.
Because I had sensed some version of this coming the night before, I had already found myself thinking about my own relationship with feedback.
I entered the rabbinate young. Very young.
And I entered it as one of the few openly gay rabbis in the country, returning to the city where I had grown up. There were very few visible models for what that life could look like, and without fully realizing it, I spent much of my late twenties and thirties trying to become an extremely competent model minority with excellent emotional regulation in the face of extraordinary vitriol.
I was attacked from both sides sometimes: parts of the gay community suspicious of anyone speaking in a religious voice at all, even a progressive one, and parts of the Jewish community treating the phrase “openly gay rabbi” like some kind of theological clerical error.
Which is a very exhausting way to spend your late twenties and thirties.
What often comes with spiritual leadership is a strange distortion field around feedback. Praise can become so effusive it stops feeling real. Criticism can become so loaded it no longer has proportion.
For years I handled both badly.
I dismissed praise almost immediately while quietly carrying criticism around internally for months like a raccoon dragging an entire rotisserie chicken into the woods.
Stoic outside, emotionally raccoon-adjacent inside.
Over time, especially as my spiritual life deepened, I started trying to relate to feedback differently. Not as verdict. Not as identity. Just information moving through the room.
Some of it true. Some of it projection. Some of it useful. Some of it absolutely none of my business spiritually.
So sitting there watching this leader absorb difficult feedback with as much openness as she could manage, I felt enormous compassion for her.
At one point she described the experience as feeling like people were throwing tomatoes at her.
After she said it, the room got very quiet.
She laughed a little when she said it, but not fully.
One person immediately reached for their water glass without drinking from it. Someone else leaned back in their chair and crossed their arms for the first time all day.
I had experienced weather shifts with this particular leader before, and I recognized the signs almost immediately. The room had suddenly taken on the same charged feeling Montana skies get right before a storm.
But I also knew something important had happened in the room. People had taken real risks to speak honestly, and I did not want the moment collapsing into shame or defensiveness.
So before responding, I quietly checked in with another facilitator in the room who worked professionally around dignity and organizational culture.
“Am I imagining this,” I asked, “or has everyone actually been incredibly thoughtful in how they’re expressing themselves?”
She agreed immediately.
And suddenly I heard myself say:
“What if these aren’t tomatoes being thrown at you?”
The room got very still.
“What if people are actually handing you heirloom tomatoes?”
Now look. Was this objectively a slightly ridiculous metaphor?
Absolutely.
But exhaustion does strange things to the human brain, and apparently mine had decided we were now doing emotionally intelligent farmer’s market imagery.
Still, I kept going.
What if people were offering not contempt, but what they genuinely believed was important insight about the moment they were all living through together? Not all of it correct. Not all of it complete. But offered with care.
Something softened after that.
Not dramatically. No cinematic breakthrough. Nobody levitated into emotional enlightenment beneath the fluorescent lighting.
But enough.
Enough for people to stay open. Enough for the conversation to continue honestly. Enough for the room to become slightly more human than it had been a few hours earlier.
By the end of the day everyone looked emotionally concussed in the way people do after sustained vulnerability.
So naturally we all went to an elegant dinner overlooking a lake.
Because apparently this is how nonprofit retreats work now: collective emotional excavation followed by artisanal appetizers.
A Jewish woman at dinner began talking with me quietly about Israel and Palestine, her own complicated relationship to Jewish identity, and the experience of building a life with her Muslim husband while trying to imagine what kind of world they were bringing a child into.
By then I thought I was off duty emotionally, but apparently the universe had other plans.
Still, there was something tender about the conversation. Less debate than longing. Less certainty than ache.
Mostly I listened.
By the end of dinner, part of the group decided to go stargazing. There was going to be a lecture, telescopes, an observatory, the full Montana cosmic experience.
Under almost any other circumstance I would have gone immediately.
But I was done receiving emotional information for one day.
So instead I went back to my room around 8:30, turned on the performative fireplace that activated with the flip of a light switch, closed the curtains, got into bed, and let the stars wait until another night.
This is Day 4 of an 8-day Montana travelogue, released one or two days at a time because apparently I process experience the same way people release prestige television now. Previous entries include bear spray theology, Glacier-induced nervous system repair, emotionally suspicious Jesus billboards, and one very performative fireplace.
If you’ve been traveling along with me through wilderness, leadership, solitude, fluorescent lighting, and the occasional existential food metaphor, I’m grateful you’re here. Subscribe, share, and send this to someone currently trying to survive modern life with their humanity mostly intact.